


Late Nights

by theinsidiouscinnamonroll



Category: Supernatural
Genre: M/M
Language: English
Status: In-Progress
Published: 2017-04-13
Updated: 2017-04-23
Packaged: 2018-10-18 13:07:27
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 5,007
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10617525
Author URL: https://archiveofourown.org/users/theinsidiouscinnamonroll/pseuds/theinsidiouscinnamonroll
Summary: A wonderful fic that my friend @desthedemon on Tumblr wanted me to post on here!





	1. Chapter 1

**Author's Note:**

> Check out the author's blog [ here](https://desthedemon.tumblr.com)!

Cas decides to go out one day. He works as a bartender so he rarely gets to go out at night. He is walking down the streets of New York, no real aim on where he is going. Just out, he takes in all the sights, looking like a tourist even though he has lived in NYC for 10 years. The color of the murky grey, cloudy sky above, and the bustling streets. And the sound of a Acoustic guitar echoing over the buildings gets his attention. As he rounds a corner that leads to the stunning waterfront, he sees a man. The man was wearing a worn leather jacket, ripped jeans, scuffed boots. And a navy green shirt. He was strumming on the guitar, tuning out the people around him, even though those people left change in the case in front. Cas knew the song, Love bites by Def Leppard, and dang did this man have a heavenly voice. His voice was one of a angel, so Cas went and listened. Throwing in a twenty dollar bill into the old guitar case. After the song finished, the man cleared his throat, Cas had spaced out in thought.

“Wha…What?” Cas stuttered, shaking his head a little as he cleared his thoughts.

“You is what. Did you mean to throw the twenty in here?” The man asked, smiling brightly Cas.

“Yes. I meant to…What’s your name anyways?”

“Dean. Dean Winchester. And no, I’m not homeless…I live in the apartment building two blocks from here. And what’s your name my fine sir?”

“My…Name…Is Castiel Novak”

“Well, Cas. I think we will be seeing each other again soon.”

 

* * *

 

 

Dean was all Cas could think about as he walked home. The meadow green eyes that Dean had rattled around in his head. “Well Cas, I think we will be seeing each other again soon?” What did Dean mean by that? Cas pondered, letting this thought float around for a bit as he walked down the wet streets of New York. It always seemed to be raining, or it had freshly rained when Cas went outside during the day. Most of the time, he saw New York at night, all the shining, shimmering lights. The lit shop windows as the reflections bounced off of the streets. The bustling streets all the time, everything was perfect. Mostly.

  
Cas must have been walking for hours before he got home. As he unlocked his apartment door, he got a glimpse of his watch. 4 in the afternoon. And he had work that night, with a squeak the door opened, revealing the small, well-kept apartment. The walls were a light, sky blue with small clouds painted on them. A box of CD’s rested near a radio on the kitchen counter. A massive bookshelf loomed with overflowing books in the tiny living room, the bedroom branched off into a small hallway with the bathroom at the end of it. Paintings lined the walls, Cas shrugged off his Trench coat and hung it on a wooden coat rack. He wandered his way over to a small, circular table where he sat down and started to take off his shoes.

“Polish, Where did I leave the shoe polish? “ Cas grumbled to himself, looking around for the small black container. He had given up when he had spotted it under the edge of his bed. That was right, he had been reorganizing things in his room, and he had set it aside for tonight. He noticed when he was working the other night that his shoes had scuffed, he normally was good at not getting them damaged. But he did every once in a blue moon. He swiftly unscrewed the lid and grabbed a old sock from a box under the bed. Cas had found that old socks work better for polishing than tissues or clothes. After half an hour of polishing, and sealing, Cas had finished the hard work of polishing his boots. Oh yes, that was quite a fashion statement, Knee high, black combat boots, Black dress pants tucked in, and a button up shirt and tie. That was his work outfit.  
  
Looking at the clock, Cas smiled softly, eight ‘o'clock, time to head into work Cas thought to himself. He stood up from his tan leather couch, stumbling a little due to tripping on the carpet. A short walk and he was at the club, Late nights. A small bar in the center of New york city, not well known, but it was what Cas called home for the night. He was greeted by smiles and people motioning to him for a refill. He yelled back at them telling him he needed to do something before he could go get the drinks. Heading to the back room, he ran into his boss, who was not looking cheerful.  
  
“CAS! WHERE THE HELL HAVE YOU BEEN? YOU WERE SUPPOSED TO BE HERE AN HOUR AGO!” Cas froze and tilted his head.  
“No sir. It’s 8 o'clock, I’m here on time. Have you been drinking too much again Sam?” Cas answered, grabbing his punch card and clocking in. He heard Sam growl softly before replying;  
  
“No Cas. I haven’t. I..Just.” The sound of breaking glass concerned Cas as he walked into Sam’s office, finding his boss on the floor crying into his knees. Cas wasn’t that good with comforting people, serving was more of his thing.  
“Sam…I’ll come back in half an hour…I need to go start up the stereo and get serving…I’ll be back” Cas rushed, making his way out of the office/back room. He picked up a random cd and shoved it into the radio. Elvis. Cas face palmed and grumbled,  
  
“I can’t fucking dig Elvis…Sam can, but I can’t” Cas punched the eject button and shoved in another cd, this time it was Def Leppard. That’s much better Cas thought, as he cleaned glasses and made drinks. Someone cleared their throat, causing Cas to look up abruptly. Green eyes, pure green eyes, milk chocolate brown hair.  
  
“Hey Cas, told you we would see each other soon”  
  



	2. Chapter 2

“D-dean…I…” Cas didn’t know what to say, he was in a trance. Dean chuckled softly and ran his hand through his short hair. Why the hell was Cas falling for this man that he barely knew? He didn’t know, it was just how his heart is going, the heart is usually right.   
  
“You didn’t what, Cas? I just came for a drink and to see my little brother” Cas tilted his head, his face scrunching in confusion, what the hell did he mean? Who was his brother? He shook his head and poured a man the drink he requested and tried his best to ignore Dean.  
  
“Cas…Do you know where Sam’s office is?” He looked up and paused. Sam…Winchester…Dean Winchester….Oh crap…His gaze meet Dean’s and he nodded. He knew good and well where it was, but did he have time to take Dean to it? No, he didn’t, and only employees could go back there. With a grumble he set down the glass he was cleaning and motioned for Dean to follow him.  
  
“This way sir” Cas said politely, avoiding eye contact, the walk down the hall was silent, the only sound was their footsteps. They finally made it to the office and that was where Cas left Dean.  
  
“Thanks, angel…” Cas rolled his eyes and swiftly made his way back to the bar. People were raising their glass to let him know that they needed a refill. He quickly refilled and cleaned glasses, not stopping for a break. He was the only bartender on that night, Sam was obviously drunk in his office, Dean was being an ass..It was going smoothly besides that, until he heard shouting. The guests of the bar looked up from their conversations and drinks, then went back to talking. A loud crash made Cas jump, he set down the glass calmly and went back to the office. Where he found Dean holding a shaken Sam in his arms, and a broken glass bottle. Dean didn’t notice him, so Cas didn’t bother asking what happened…He just left and went on with his job..This week is gonna be a pain in the ass Cas thought to himself, groaning at the thought.


	3. Chapter 3

Finally, It was 5 in the morning, the bar was closing, the guests leaving, and Cas. Cas going home after a long night, even longer since he was still shook from Dean’s presence. How stupid of him not to realize the connection between Dean and Sam. He didn’t notice it because some people had the same last names, and weren’t related. But Winchester was one of those uncommon last names. So he should have connected the dots. Shrugging his worn out tan trench coat on, and clocking out again he started to head out. Pausing only briefly to think about if he should check on Sam, or not. Cas decided it was best not to, after all, he wasn’t part of Sam’s family, why should he get involved. **  
**

The streets were bustling with the early birds, the sound of honking horns, and running engines was everywhere. The newspaper stands filled with people, the coffee shops flicking on their open signs. This is what Cas loved about walking home after work, he got to see the city wake up. Florists setting up their flowers and watering them. Food carts starting their rounds around the big city. Tourists spilling out of hotels with their cameras and excited faces. Cas reached his apartment, which had a excellent view of Central park. The sky was a crimson orange, reddish color; with a hint of purple in it. The clouds breaking apart slowly to reveal the sun. Cas smiled, slowly removing his trench coat and throwing across the back of a chair.

Cas bit his lip in thought, looking at the sunrise with intent. Memories of the past zipping around in his brain. One memory of his best friend, who committed Suicide a long, long time ago. Another of his mother, who died in a car crash. And his father, a man who was gone most of the time, and a drunk whenever he was home. A gambling man. Then his three brothers, Gabriel, the trickster of the family. The number of pranks that were pulled, the thought of them made Cas chuckle. Lucifer, the misunderstood one. He often had a bad temper, but always protected Cas from harm, he wasn’t about to let anyone hurt his little brother. And then there was Micheal. The oldest brother out of the four of them. He was too serious, but he was smart and reasonable. The thought of his family made Cas’ heart drop. He hadn’t seen any of them in years. Trying to dismiss the thought, he looked away from the window and turned to the large stereo system beside him. With a grin, he looked at the cd rack and chose Dio.

Dio was one of his favorite bands in fact. Heavy metal usually wasn’t his thing, but something about the sound of the leader singer got him hooked. “Holy Diver” started, the eerie beginning filling the small apartment. His neighbors would say the music was satanic, but who cared? Cas didn’t, as long as the music was good, he couldn’t complain. The sound of the doorbell scared him, scrambling to turn off the radio, Cas stood up. Making sure he looked semi presentable, he walked to the door and opened it. Only to see Sam, leaning against the doorway, his brother walking quickly down the hall.  
  
“Sam? Why are you here?” Cas said, concern piercing his voice in an instant. All Sam could manage was a few huffs and strangled sob. He looked over his boss’ shoulder to look at Dean, who looked concerned.   
  
“Come in…Come in, uh..I’ll get you guys something to drink…Is orange juice fine?” Dean nodded and walked Sam through the door past Cas and to the table. Now Cas was really worried, what the fuck was wrong with Sam. And why did he go to Cas, him out of all people. Shutting the door, he walked to the small kitchen, which was terribly out of date. The light blue, 50’s looking fridge was tucked away in the corner, looking softly at him. With light tug, he opened it, pulling out the container of juice, then shutting the fridge afterwards. He reached up to a cabinet and got out two glasses, pouring the orange juice then putting the juice away. He made his way carefully out of the kitchen and to the table, where Sam was sobbing with his head in his arms. Dean, rubbing his back lightly and looked up at Cas’ approach.  
  
“Sorry for coming without notice..Sammy insisted you would be the best person to come talk to..” Dean started, stopping to rub Sam’s back again. Cas tilted his head, and opened his mouth to speak, then shut it quickly, thinking more about what he was going to say. To come talk to him about what? Cas wasn’t good with comforting in anyway possible, and Sam knew that.   
  
“To come talk to me…About what exactly?” Cas mumbled, looking at Dean in confusion. Dean looked Cas in the eye and said;

“He…I mean..” Dean shook his head, then started again “Two things actually. HE fell in love with a dude. He said that you were…You know….Gay…And said that maybe you could help him with his feelings and Two, our parents…Just…Uh” Dean blinked away tears, rubbing his eyes then continued, “Just..Passed away, their house caught on fire…And…They didn’t get out in time..”


	4. Chapter 4

Shit..Shitshitshitshit, was the only thought on Cas’ mind. Why the fuck did they think it was a good idea to come to him for this. FOR FAMILY SUPPORT…HOW THE HELL. Cas ran his hand through his hair and took a long, deep breath. Okay, be calm Cas, get back on the horse. If you freak out, they will freak out even more.   
  
“I’m..I’m sorry for your loss….Do you need a place to stay for the night?” Cas said, watching Dean closely rub Sam’s back. The way he carefully made movements, like Sam could snap in half at any moment. The small circles he would make every so often, and Sam relaxing with every movement. They obviously had a deep connection, Cas could tell that they needed each other, for emotional and mental support. But Dean didn’t know what to do about his brother being gay, that was one crystal clear thing. Was Dean homophobic? He hoped not, but that obviously wasn’t the case. He spoke softly to Sam, whispering into his ear, most likely reassuring him everything was going to be alright.

“If it isn’t a bother, then yes, we do..” Dean stammered, his voice cracking slightly then recovering like it never happened. Cas let that sink in, taking in Dean’s facial expression. The hurt, pain, the lost look in his meadow green eyes. The way his face softened as he turned to Sam again, the lost, pained look washed away, and was replaced with a caring one. For someone going through emotional times, Dean was holding his ground in the battle. Not budging one bit, was it because he needed to stay strong for Sam? Or did he not feel, was he just stone cold? Whatever the case was, Cas didn’t dare ask. It was Dean’s business after all, and he didn’t know the man well either. Yet he insist, to let them stay at his apartment. Over his head, maybe, concerned? One hundred percent.

Cas pulled up another chair to the table, and tried not to disrupt anything. Sam looked up at Cas’ arrival, eyes wide with shock, not to mention terribly red from crying. A sound that sounded like a dying cat caused Cas to look up abruptly.

“Cas..I-i’m sorry for coming without notice…And, I…” Sam stammered, before taking several deep breathes, his hands trembling on the table. How broken up was Sam, and which topic was he broken up about more? Him falling for a man? Or his parents dying? He knew from long talks with Sam, most of which of Sam was drunk. And Cas, perfectly fine, not even having touched a beer. They had many of these types of lonely nights, Sam, the one spilling out secrets that he had never told anyone. Sam didn’t think about what he was saying half the time. Leaving Cas puzzled after each teeny snippet of a story. Most of which were tragic, graphic and disturbing. Their father a drunk, who was never home that often, and beat his kids whenever he was. Sam told tales of how his brother had taken more beatings for him then he could count. He explained and showed Cas all the scars from those beatings. He remarked about how that his brother probably had more scars then ANYONE he had ever known. Each visit, left Cas with a part of Sam’s story. One that he was slowly connecting the dots on.

“Sam…Sam..It’s fine. It’s not a issue..I always have that spare room open, remember? Remember all the nights you have come without me knowing ahead of time? When you come to my door at two o’clock in the fucking morning? And I’m here, always here…Anything for the Winchesters.” Cas stated, looking Sam right in the eyes, not breaking the contact till Dean cleared his throat loudly.

“No chick flick moments please. Or at least anymore. Speaking of which, I know it’s late..And Sam here is probably gonna fall apart at any moment from stress and exhaustion. I’m assuming Sam knows where this spare room is?” Sam looked at his brother and nodded, stumbling up and out of the chair. His boots scuffing against the wooden floor of the dining room. Cas opened his mouth to his something, but bit back the words. They were spread thin already, and Cas didn’t want to interrupt the brotherly moments the Winchesters were having. With a glance around, he took the empty glasses, which must have been drank when Cas wasn’t looking and went to the kitchen sink. The air temperature was quite warm, warmer then Cas thought it was originally. He heard the hushed tones of Dean and Sam faintly as the glass clinked together in the sink as he set them down.

And there it was, the wave of stress, nervous and panic washed over him like a tidal wave. Cas bent over the kitchen sink, his hands gripping the metal edges. He couldn’t do this. How could he do this? He didn’t know how to help people. He was useless, he couldn’t feel anything. He was broken, a lost, broken, wingless angel in a abyss. A alone angel in a crowd demons, wearing a mask that had a face of a demon. And everyone assumed he was one too. They didn’t see what was going on underneath the surface. No one ever did. He wasn’t a good people person. In fact, he never really was. He was socially awkward, but that didn’t stop him much from making friends with people. And he was glad that he still could. The soft footsteps of someone behind him made him freeze.

“Cas..Are you alright there, buddy?” Dean whispered softly, coming up beside the dark haired man. Cas didn’t answer, he just kept staring down at the sink.

“Sam has told me a lot about you Dean. All the beatings you took for him, all the scars you have. Stories of how you stole your dad’s car, and still have it to this day. How he sent you the title to it. The black 1967 chevrolet impala. Dean. I know a whole of your background. I just don’t know you personally. And, I would like to change that, just not right now. Not when Sam is like this, drunk and not doing so hot.” Cas muttered, Dean being completely silent, causing Cas to look up at him. Dean was nodding, obviously thinking about the past, until he noticed Cas looking at him.

“Yeah..Yeah…That…I’m gonna hit the hay…” He pointed to Cas’ couch, and flopped down on it. Crossing his arms across his chest. Oh hell…What did Cas get himself into. Without another word, Cas strode down the hall to his room and shut the door behind him, slumping against it, he took off his shoes, unbuttoned his shirt, stripped his jeans off and flopped down on his soft mattress. Hoping that tomorrow Sam would be able to talk properly.


	5. Chapter 5

The stars were shining brightly when Cas woke again. Groaning he rolled over and looked at the clock on his nightstand. 3, in the morning. It wasn’t a known thing that Cas could sleep with other people in his house. It was unnerving for him, it was that they weren’t people he knew. It was just that, he could hear the movements that they made. Or the words they spoke if they talked in their sleep. Rubbing his eyes, Cas threw on a T-shirt and a pair of sweatpants and to the kitchen. Not turning on any lights, not wanting to disturb Dean, who was asleep on the couch.

* * *

 

**Dean’s POV**

If Cas was trying to not wake him up, it wasn’t working that well. Not because he wasn’t being quiet, not because he wasn’t turning on lights. It was due to that Dean never went to sleep, he was just staring up at the ceiling blankly. Thinking about what god was trying to tell him, god at this point, probably hates him. He was bisexual, and people always kept telling him that he was ‘confused’. He wasn’t confused, and he wasn’t queer. He was Bisexual, he didn’t understand why people say things like; “Why can’t you choose?”, “So you like Guys? Then why aren’t you gay?”, “You’re straight right? Because you like girls?”. It pissed him off, yes, he likes both, he just leans towards guys more. Slowly, he shifted on the couch so he was sitting upright, looking over at the faint outline of Cas as he did something, most likely getting a drink of water, as he heard the tap running. Damn it, Dean. You barely know the guy, yet here you are, tripping head over heels once again.

Why are you like this, Dean? Why is it always the shy ones, the ones who will never talk that much?  Dean was mentally beating himself when he heard a low “ow” from in front of him, causing him to look up and see Cas looking at him.   
  
“S-sorry….Did I wake you Dean?” The dark haired man said softly, sitting down on the table in front of Dean. How was he supposed to answer this correctly? He couldn’t say no, I was just thinking about your shy smile..Hell no, you didn’t wake me up, I was just thinking about the way you walk…  
  
“Dean…?”  
  
“Oh..Sorry…No, you didn’t wake me up..I was just-” He cut himself off before he could say anything else. He could see Cas’ head tilt even in the dark. How confused he was at his unfinished sentence. Then his mind decided to start thinking about that day’s events. His parents were dead, not coming back ever. He was glad his father was, that man who was gambler, who Almost sold Sammy to a pervert once, only he was too drunk to finish the deal. Dean hated his father with a burning passion,  he hoped that man ended up in hell. Hoping that he was with Lucifer, being tortured endlessly with no end to the pain. Or maybe his father was the devil, so he was sent back to the cage.

“You just, what Dean? Dean..Dean, are you crying?” Cas’ tone was laced with concern, even Dean didn’t know he was crying. His thoughts had drifted to his mother. A literal Angel, so caring..She was the best mom anyone could ask for. She went to every one of Sam’s plays that he was in when he was in high school. She bought Dean his guitar, the one that he was playing the day he met Cas. He has had that guitar since he was given it for his 14th birthday. Just a simple Acoustic, strap, tuner, pick, etc etc..He had painted the lyrics of “carry on wayward son” by Kansas on it when he was 18. To show that he carried on, and kept going to adulthood.

The draping of a blanket around his shoulders scared him, shaking him from his thoughts. He looked around and saw Cas putting a blanket around him and handing him a box of tissues. Damn, did he space out that much in thought? Dean accepted the tissues with a nod and a weak “Thank you”. More tears swelling up in his eyes.

“Hey Cas…I…Must ask, do you like my little brother?” Dean blurted out randomly, that was a thought that was on his mind. How many times had Sam come over to Cas’ place? Enough that Cas always had the spare room always made and ready. This obviously took Cas by surprise as he took a deep breath before saying anything.

“No. I don’t like him in a Romantic way. Just in a friend way” Cas stated, looking Dean straight in the eye, or that’s what he was probably doing. Dean didn’t push the question any further, not wanting to get into the man’s personal life.

“Okay then..What’s your favorite color?”

“Green. Green like the color of rolling meadows, nice and bright, but also dark in some areas. Like the color of tree leaves. Or a well kept lawn. That’s the color of green that’s my favorite. What’s yours Dean?” Castiel asked, a hint of excitement in his voice.

“Mine? Um…” Shit. BLUE..But the color of Cas’ eyes..”Blue..The color of a clear sky, or like the waters of the atlantic ocean. But sometimes I like a good Stormy color of Blue…So just…Blue in general I guess.” He was making progress with Cas, maybe they will have something in common..


	6. Chapter 6

**Dean’s POV**

He was getting somewhere with Cas, finally! He didn’t try to flirt, in fact. Sam thought he was one of the biggest flirts that he ever knew, his little brother didn’t know he was Bisexual. Sam thought Dean was straight like a fence. But, Dean was a fence sitter, he wasn’t the planks of wood that made up the fence. The truth was, he had battlescars. Not just scars from his father, he had emotional ones. Ones where he was at war with himself over his sexuality. That war has scarred him, his father only added salt to that wound. How he went on how Dean could never find love. How he cried himself to sleep half of those nights.

Shooing those thoughts away, he focused back on Cas, trying to remember where he left off. Then Cas asked him another question, damn, this was starting to feel like twenty one questions..

“What’s your favorite animal, and don’t say cat or dog.” Dean had to think about this more closely, he never really had a thing for dogs. They stunk up cars, Cats were cute, but they were little devils. Dean loved foxes though, they were cunning, fast and light footed. They could get away with anything they wanted. Wolves were a close second, they could be silver streaks in the night, howling at the lonely moon while the stars shine brightly. Dean bit his lip in thought before answering,

“ Foxes. Red foxes are my favorite, but arctic foxes are also pretty epic.” The excitement in Cas’ eyes was more obvious now, the corner of the other man’s mouth twitching into a faint smile.

“ Foxes. Huh, I thought you would be more of a lynx, panther guy. Wasn’t expecting you to say fox. Well, my favorite animal is gotta be a Raven.” A bird of Death, that was fitting. Cas seemed like the type to have tricks up his sleeve. A simple man, but a devious one at that. His turn to ask a question, he had to make it a good one. Will you go out with me? No, Dean bad. You don’t fucking know the man at all. Don’t over step the welcome. What’s another interesting question, how about what city in the U.S is your favorite? Yeah, that sounds like a good one to ask.

“Cas, what’s your favorite U.S city? Mine’s Portland, Oregon. I love all the bright lights, the bridges that connect the city together, the MAX train. The food, shops, and the towns around it. The nike Campus down in Beaverton…” Dean cut himself off before he could continue rambling. He heard shuffling from another room and a meek voice squeaking “Dean? Cas? Dean? Dean, Where are you?” It was Sam, who wandered out into the small living room.

“Oh, Hey Sam, yeah me and Cas are here.” Dean answered, clearing his throat moving on from the very gay moment that he and the strange man had. What the hell was wrong with him? He heard Sam sniffle a little and sit next to him. The large puppy snuggling into his brother.

“Hey, Sam, are you feeling better?” Cas asked shyly, flicking on a lamp, the room now in a soft glow of light. Sam rubbed his eyes briefly before answering;

“Yeah. Only by a little though, and did you purposely make my room smell like cookie dough?”

Cas stiffen a bit, his shoulders raising up. He shook his head and excused himself to the bathroom. What the fuck? Why did Cas get nervous when Sam said that?


End file.
